An IM Infatuation Turned to Romance. Then the Truth Came Out.

Photo Illustration: Christopher Griffith

Every morning of every weekday for 12 years, Thomas Montgomery punched in at the Dynabrade factory in Clarence, a small town in upstate New York. He strapped on his goggles and stood at his machine until the late afternoon, churning out components for power tools. After work, he walked the family dog, Shadow, and took his two daughters to swim practice. He became such a regular presence at the local swim club that he was named its vice president. He tried to be a good father and a decent husband to his wife of 16 years, Cindy. There were a few things he enjoyed — poker night on Fridays with the guys, playing Texas Hold 'Em on Pogo.com, and the Dynabrade euchre tournament, which he dominated for two years in a row. For the most part, though, life was uneventful.

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Which may be why Montgomery looked at himself — a 45-year-old former marine with a reddish mustache, bulging gut, and disappearing hair — and decided to become someone else. That person, he wrote on Dynabrade stationery that he stored in his toolbox at work, would be an 18-year-old marine named Tommy. He would be a black belt in karate, with bullet scars on his left shoulder and right leg, thick red hair, and impressive dimensions (6'2", 190 pounds, and a "9" dick"). Emboldened by his new identity, Montgomery logged onto Pogo in the spring of 2005 and met TalHotBlondbig50 — a 17-year-old from West Virginia, whose name, he later learned, was Jessica.

He began instant-messaging "Jessi," who later also went by the handle "peaches_06_17," and the lies flowed easier with every press of the Return key. His mom had died of cancer when he was 12, he told her, and his father was a military man. At 17, Tommy had raped a cheerleader, and his life became so hopeless that he enlisted in the Marines. After a stint at boot camp in June to train as a sniper, he was headed to Iraq. Montgomery concocted elaborate ruses to maintain Tommy's cover story, creating a second identity as Tommy's dad, Tom Sr., who bore a striking resemblance to the real Montgomery. Tommy's access to the Internet was supposedly limited because of his military duties, so Dad, as Jessi soon referred to him, began shuttling messages between the two lovers. He also told Jessi to send any mail and packages for Tommy to him, because he had contacts in Iraq and could get them to the young marine quickly.

Tommy's tales of hard luck drew Jessi in. He was in need of comfort, and Jessi provided it, saying she was proud of him despite his mistakes. Tommy responded by telling her that she was "the best thing that ever happened to him." As their intimacy grew, he sent her a picture of a young marine, claiming it was himself, and confided that he planned to commit suicide in Iraq; she made him promise to stay alive for her. They talked on the phone when they could. But if Jessi couldn't reach Tommy, she sometimes IM'd Tom Sr. to talk about her lover. Jessi also emailed Tommy photos of herself, care of Tom Sr. She lived up to her screen handle, whether she was running her fingers through her flowing blond hair or wading in a pool in a yellow bikini or showing off her long tan legs in a denim miniskirt.

Jessi fell for Tommy, and Montgomery did, too — or, at least, for the idea of himself as Tommy, a young man on his way to a future with the prettiest girl around. Tommy told Jessi that he'd had their special motto — the Marine saying "Always and Forever" — tattooed on his arm, along with her name encircled by a heart. Jessi, for her part, crafted video montages of herself for Tommy that were set to power ballads like Aerosmith's "I Don't Want to Miss a Thing" and Lonestar's "I'm Already There."

Jessi's photos provoked the couple's first major blowup: Montgomery became convinced she'd sent her pictures to other online admirers and accused her of betraying him. To apologize, Jessi sent him a snail-mail letter, enclosing one of her G-strings and a sterling silver "key to my heart" chain. She signed off the missive with "T&J" inside a heart. Tommy forgave her, but Montgomery, in his role as "Dad" and occasional intermediary, did not. She defended her mistake, writing in frustration that Tommy "has let it go why wont you." Tom Sr. wrote, "because u will hurt him and hes an idiot and will believe ur lying ass."

Meanwhile, Jessi and Tommy had settled into a routine, talking by phone between 6:30 and 6:40 am and from 3:30 to 3:40 pm, when Jessi was led to believe that her "sweet sexy marine" was off duty. By Christmas, about eight months after they met online, Tommy proposed marriage and Jessi accepted. He sent her poinsettias, and she sent him more G-strings and dog tags engraved with the message TOM & JESSI ALWAYS & FOREVER. Jessi worried constantly about Tommy's safety, writing, "I know your being careful honey and you have the best with you but I also know anything can happen." Anticipating his return from Iraq, Jessi planned for their first night together, expressing nerves about what would be her "first time." She ended on an optimistic note: "Won't be long until its Jessica Blair Montgomery."

Montgomery was consumed by his marathon online chats with Jessi. While at work, he didn't stop talking about her, telling colleagues that he planned to leave his wife and move to West Virginia. In the evening, he would chase his daughters off the computer, planting himself in front of the screen late into the night. Cindy couldn't compete with his new obsession.

For New Year's, Montgomery made a resolution, which he scribbled on his work pad. "On January 2, 2006, Tom Montgomery (46 years old) ceases to exist and is replaced by an 18-year-old battle-scarred marine," he wrote. "He is moving to West Virginia to be with the love of his life." He vowed that he would set aside enough of his imaginary millions to care for Cindy and the girls, even as he fantasized about the life he would build with Jessi. When the new year began, however, he was still stuck in his aging body and stale life. He wrote in frustration, "I wish I would know the exact time I would change to new Tom to prepare for it."

Cindy did not know about her husband's double, or rather triple, life. But she did know that something had changed inside her two-story yellow house. "He wouldn't get off the Internet," she said. "It gave him access to something he wouldn't have had otherwise." Then, in February 2006, she discovered some of Jessi's mementos and unraveled the truth. Cindy's marriage might not have been the happiest, but contending with the layers of deceit she uncovered — not to mention a teenager's lingerie — was too much. "What I cannot believe is that you are living out some bizarre fantasy — as father and son," she wrote in a note to her husband. "If you want to separate — We can… but to continue to lie to me & the kids while she is sending 'your son' gifts in the mail is not acceptable."

The couple stayed in the same house, though Montgomery complained to a coworker about being consigned to the basement. As a mother, however, Cindy felt she had to do something for Jessi. She wrote a letter, enclosing a recent photo of her family. "Let me introduce you to these people," she said, describing her husband, Tom, her daughters, 12 and 14 years old, and herself — the "c," as she put it, in Montgomery's many emails to Jessi from their account named "tcmontgomery1." There was no son, she told Jessi, only her husband, a 46-year-old former marine. "From what I am pulling from your letters you are much closer to [my daughter's] age than mine let alone Tom's," Cindy wrote. "Are you over the age of 18? In this alone, he can be prosecuted as a child predator." Adding that Jessi could be her own daughter, Cindy offered some maternal advice: "Do not trust words on a computer."

IM transcript, April 17, 2006

Jessi didn't know who to believe. Was there no Tommy? Or had Cindy invented the story because she wanted Tommy for herself? Jessi found a friend Montgomery had mentioned who also frequented Pogo: "Beefcake1572," or Brian Barrett, a 22-year-old student at Buffalo State College who worked part-time at Dynabrade with Montgomery and played poker with him.

When Barrett confirmed his friend's trickery, Jessi was devastated. How could her "everything," as she referred to Tommy, be a nothing? She turned to Barrett for solace, playing Lottso, a kind of Bingo, with him in the Princess Priceless room on Pogo and IMing him on Yahoo. Their conversations quickly turned intimate. Soon, in public forums online, she and Barrett called Montgomery a child predator and taunted him. Montgomery was suspended from a game room. She shared her passwords with Barrett, who would log onto her accounts and talk to Montgomery as Jessi to humiliate him. At work, Barrett boasted about his new relationship.

Montgomery was furious. "Half the company" thought he was a "fucking loser and predator," he IM'd Jessi. Parents no longer trusted him with their kids. His life was so destroyed that he appeared to be contemplating suicide. "U can say goodbye forever to me and Tommy," he told Jessi.

IM transcript, May 20, 2006

Despite her own anger, Jessi couldn't turn her back completely on Montgomery. He was all that remained of her lost Tommy, after all. "If he existed I would still be holding him everynight and sharing dreams with him everynight," she wrote Montgomery. He remarked bitterly that she could "fill that void" with a different admirer. But Jessi continued to placate him, saying, "I ache to be with Tommy," noting that the 18-year-old existed in Montgomery's continued love for her. Jessi promised Montgomery she would stop talking to Barrett, saying she took up with him mainly to get revenge. Her existence was a "living hell," she said, and she just wanted "everyone to hurt" like she did.

Despite her promises, Jessi continued her romance with Barrett. Her conversations with him reflected ordinary teenager hang-ups: She complained about her mother, talked about her preparations for prom, and chatted about her part-time job as a lifeguard. Their sessions often ended with Barrett typing one-handed while Jessi urged him on with comments like "can I kiss something long and hard." At first, Jessi wanted to hide the rekindled relationship from Montgomery, but Barrett persuaded her to go public, and they posted about each other in their online profiles. As they anticipated, Montgomery noticed immediately. "I cant believe u chose her over r friendship," he told Barrett. "U wanted her u got her just tell her to leave me the fuck alone."

Jessi seemed torn between the two men. When Barrett wanted to visit her during his vacation, she told him not to come. While he was away and offline, she turned to Montgomery again, telling him that she planned to break up with Barrett. Montgomery heaped abuse on her. But he finally agreed to forgive her if she promised, yet again, never to lie to him about Barrett. "If I find out any lies were told to me u will lose something very close to u," Montgomery warned her.

IM transcript, May 27, 2006

He was training, he told Jessi, for "war." But he wasn't going to Iraq. For the first time in 15 years, Montgomery was working out; every day, he ran 5 miles and spent two hours at the gym. He began making vague threats at work. One employee was so jittery that he donned a bulletproof vest as a joke one day.

Montgomery and Jessi couldn't pull away from each other or their computers. They spent so much time online "as friends" that Montgomery was barely sleeping. He showered Jessi with attention, and she enjoyed the adulation. If he wasn't engaged in intricate analogies about his "snake" in her "wv [West Virginia] fox," he was professing his love. But time and again, his affection would veer toward violent jealousy at Jessi's online boyfriends. He repeatedly threatened to post Jessi's home address online so that the "niggers" could find her easily. Even as she talked him down, Jessi seemed to thrive on the whiplash. Whenever Montgomery threatened to "delete" her from his life, she begged him not to.

In late summer 2006, Montgomery found out that Jessi and Barrett were talking again. The cycle of invectives began anew. Nothing seemed much different at first. But then, after days of futile attempts to appease Montgomery, Jessi went quiet. On September 13, 2006, he IM'd her at 1:33 in the morning, telling her "u r a whore and thats all u will ever be." She wrote back "im leaving now" and signed off. Montgomery sent her several more messages throughout the day, to little response. The next day, he pinged her again: "hey whore u suck ur bf brians cock today." The white IM window stared back at him. The following morning, on the 15th, he called her, waking her up. He was screaming, she says, and in an uncontrollable rage. She hung up.

Later that evening, at 10:16 pm, Barrett punched out of work and walked to his white pickup truck in the Dynabrade parking lot. He swung open the door of his truck, settling into his seat. Three shots pierced the driver's side window, and Barrett slumped sideways. He'd been shot in the neck and upper arm by what police believe was a .30-caliber carbine rifle.

IM transcript, September 13, 2006

Just before midnight, Montgomery was at his computer. "U waiting for ur bf," he wrote. At 2:15 in the morning, he tried again, writing "come on cw ur bf brian wont mind u talking to me." In interviews with detectives several days after the murder, tipsters fingered Montgomery as the likely culprit. He'd been bad-mouthing Barrett, and his behavior had grown increasingly erratic. According to the detectives, a coworker said that Montgomery told him "he wouldn't be stupid enough to leave shell casings lying around if he were to kill someone." While standing at the time clock two weeks before the killing, Montgomery had asked that same employee what time Barrett got off work.

When detectives later examined Barrett's cell phone, they found Jessi's number. Lieutenant Ron Kenyon called her in the middle of the night to confirm that she'd had an online relationship with Montgomery and to warn her that she might be in danger. He then sent a message to her local police department in West Virginia, requesting that a cop go to Jessi's home at the address she'd given him.

Officer J. L. Kirk arrived the next morning at a dingy white house next to an automotive-parts dealer. But Jessi wasn't there. Her mother, Mary, said that the teenager was away and that she had no way to contact her. Kirk reported back to Kenyon, who insisted that he'd just spoken to Jessi a few hours earlier and that she had to be in the house. Kirk continued questioning Mary, whose manner struck him as strange. The more he pressed, the more nervous she got until she finally "came clean," as Kirk put it. She was the woman Kenyon had spoken to. In fact, she was the woman Barrett had fallen so hard for. And yes, Mary was the woman Montgomery may have killed for. She'd used her daughter's identity to beguile the two men.

Back in Buffalo, Kenyon couldn't believe that the Jessi he'd talked to was really her mother. "She was very convincing," he said. "She sounded like an 18-year-old girl to me." He drove to West Virginia to see the truth himself — that the lithe 18-year-old blonde of Barrett's and Montgomery's fantasies was a plump 45-year-old married mother of two with short brown hair.

When he was questioned about the murder, Montgomery told detectives he needed to retrieve his lunch from his car, because his peaches would spoil. The cops noted his taste for that fruit: A peach pit — which later tested positive for Montgomery's DNA — had been found next to Barrett's truck. A leather cartridge case with dog hairs that they surmised belonged to Shadow was found in the same area. In addition to Jessi's G-strings at the Montgomery house, police also unearthed a photo of his gun cabinet containing a .30-caliber rifle, now missing from the cabinet. At the time of the questioning, Montgomery had no idea he'd been conned by Mary.

On November 27, police arrested Montgomery on murder charges. He denied killing Barrett, saying he'd gone to a local restaurant and arrived home between 10:00 and 10:10 pm, before the killing took place. His wife estimated that he arrived a half hour or more later. Montgomery's cell phone records also put him in the vicinity of Dynabrade at the time of the murder. Furthermore, investigators intercepted a call that he placed to his wife from prison that seemed to suggest the cartridge case was his. Of course there were dog hairs on the cartridge case, he told her. Didn't she remember the state of his car?

Then there was the matter of the hundreds of pages of correspondence and dozens of photos he kept on his computer to document, and savor, every moment of his time with Jessi: It was a digital paper trail showing a man careening out of control. Ken Case, the assistant district attorney who worked on the case, said, "He was a guy who prior to this happening was a very dedicated father. To make that much of a transformation, as a result of communicating with a fictitious person, is pretty frightening."

When I caught up with Mary outside her home, she strode to the family van in the driveway and took off, then hit the brake abruptly to ask me who I was. She wore a gray T-shirt, jeans, and black flip-flops; her nails and toenails were perfectly manicured. She burst into tears at the mention of Barrett's murder, her French tips and diamond ring glinting in the sun as she pushed a crushed paper towel under her sunglasses to dab away the tears. She begged wired not to use her last name.

Locals say she was "one of the best parents around" and a devoted cheerleader at Jessi's basketball and softball games. The principal of the middle school that her children attended was so impressed with Mary and her maternal dedication that he hired her for part-time clerical work. In all of Jessi's 18 years, Mary told me, she had missed only one of her daughter's games, to work the polls at election time. How could a mother like that, I asked her, hijack her daughter's identity to seduce strangers? Her answers, unsatisfactory as they are, suggest a profound capacity for self-deception.

Mary said she joined Pogo a few years ago to relax and kill some time. It was only after she paid for the membership, however, that she realized she'd used Jessi's screen name. Mary was directed to a teen room, and she never bothered to correct the mistake. She didn't intend for her many admirers to fall in love with her.

Nor did she fall in love with any of them; she says she is happily married to her husband of 23 years. Brian was a "sweetheart" and when he initiated the flirtation, she didn't know how to discourage it without revealing her true identity. Tommy, she said, "was a child who needed someone to show him they cared."

Why, then, did she continue talking to Montgomery once she knew Tommy didn't exist? She says she worried he would take advantage of a real 18-year-old. "I should have just let it go," Mary conceded. But she didn't, and then she had to keep talking to him to prevent him from doing harm — first to himself, it seemed, and later to her own family members.

That's the story, more or less, that Mary seems to have told her daughter, whom she refers to lovingly as "my princess"; her husband; and, after boarding a plane for the first time in her life, the grand jury in Buffalo.

Montgomery spent the summer awaiting trial at the Erie County Holding Center in downtown Buffalo. The beefy 200-plus-pound man in his mug shot had disappeared; he wore round wire-rimmed glasses, and his orange uniform hung from his now-frail frame. He tried to commit suicide in April, he said, after receiving a letter from his daughters stating they wanted nothing more to do with him. His marriage to Cindy fell apart, and she stopped visiting in March.

He tried to explain what drew him to his computer. "When I'm talking to Cindy or you like this, face-to-face," he said, "it's hard for me to say what I feel." As Tommy, however, the words came easily. And then there was Jessi. He loved her, or at least believed he loved her, though he knew he was "never going to meet her." His plan was to "kill Tommy off" in Iraq, but Cindy intervened too soon. He nearly committed suicide because of his guilt about having lied to Jessi. Why, I asked, when he was suspicious of so much of what Jessi said, did he believe she was who she claimed? "She kept sending pictures," he explained. "One picture, maybe not. But there were so many pictures over a period of time."

Montgomery insisted he wasn't the killer. He claimed Barrett was getting calls at work from lots of people who didn't like him, an argument he said will be central to his defense. Montgomery added that when Jessi first met Barrett he was happy for her — happy that she'd managed to find someone her own age.

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